Facile strategy for obtaining luminescent polymorphs based on the chirality of a boron-fused azomethine complex

Abstract

A chloro-substituted boron-fused azomethine complex (BAmCl) having a stereogenic boron center was synthesized for obtaining a luminescent chiral crystal. We succeeded in isolating the (R)- and (S)-enantiomers of BAmCl and preparing the homochiral polymorphic crystal, while we obtained the racemic crystal with rac-BAmCl. Single crystal X-ray diffraction analyses suggest that a variety of intermolecular interaction patterns and intrinsic flexibility of the molecular framework should play a significant role in stabilizing the homochiral crystal. We found the difference in molecular arrangements between the racemic and the homochiral crystals, and we observed distinctly different emission colors. In particular, we observed heat-initiated homogeneous racemization without the need for a solvent or catalyst in the molten state of the homochiral crystal (R)-BAmCl. Our results mean that chiral resolution of a flexible fused-skeleton having a stereogenic boron center can be a platform for creating luminescent polymorphic materials.